Reaction of 2-cyano-3-(4-oxo-4H-chromen-3-yl)prop-2-enamide with some phosphorus reagents: synthesis of some novel diethyl phosphonates, 1,2,3-diazaphosphinanes, 1,2,3-thiazaphosphinine and 1,2-azaphospholes bearing a chromone ring
| Autor: | Tarik E. Ali, Mohamed M. Hassan |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Reaction mechanism
010405 organic chemistry Phosphorus chemistry.chemical_element General Chemistry 010402 general chemistry Ring (chemistry) 01 natural sciences Phosphonate 0104 chemical sciences chemistry.chemical_compound chemistry Reagent Chromone Phosphorus tribromide Organic chemistry Phosphorous acid |
| Zdroj: | Research on Chemical Intermediates. 44:173-189 |
| ISSN: | 1568-5675 0922-6168 |
| DOI: | 10.1007/s11164-017-3096-z |
| Popis: | Novel chromonyl phosphonic acid 3, diethyl chromonyl phosphonate 4, and diethyl chromonyl pyridinyl phosphonate 5 were obtained from treatment of 2-cyano-3-(4-oxo-4H-chromen-3-yl) prop-2-enamide (2) with phosphorous acid and its diesters. Also, an efficient route to functionalized phosphorus heterocycles such as 1,2,3-diazaphosphinane, 1,2,3-thiazaphosphinine and 1,2-azaphosphole bearing a chromone ring was achieved via reaction of compound 2 with some phosphorus sulfides and phosphorus tribromide. A key part of the reaction mechanisms is discussed. Structures of the new synthesized products were established on the basis of spectral data (IR, ESI-MS, 1H-, 13C and 31P-NMR spectra). An efficient route to functionalized phosphorus heterocycles such as 1,2,3-diazaphosphinane, 1,2,3-thiazaphosphinine and 1,2-azaphosphole bearing a chromone ring was achieved via reaction of 2-cyano-3-(4-oxo-4H-chromen-3-yl)prop-2-enamide with some phosphorus sulfides and phosphorus tribromide. |
| Databáze: | OpenAIRE |
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